Tetrahedron p. 3285 - 3289 (1982)
Update date:2022-08-03
Topics:
Wartski, L.
Bouz, M. El
In order to synthesize γ carbonyl aldehydes which are interesting precursors in organic synthesis, we examine the action of masked acylanions, the lithiated derivatives from 1,3-dithiane 1a and 2-phenyl-1,3-dithiane on selected unsaturated aldehydes: crotonaldehyde 2, cinnamaldehyde 3, 3-methyl butenal 4 and methacrolein 5.In THF 1a leads with the four aldehydes to allylic alcohols.However 1b gives products resulting from C=C and C=O additions.Using THF-HMPA, we show that C=C addition is generally enhanced.Furthermore, in all cases examined C=C and C=O addition take place under kinetic controll: the regioselectivity observed can be interpreted by repulsive interactions due to the substrate and the reagent structure as well as lithium-carbonyl compound interactions.
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Doi:10.1039/j39660001519
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